Arts & Entertainment

For more than two decades, Rob Van Winkle has been the butt of jokes and the subject of parody. But the man responsible for the 1991 Grammy-nominated "Ice Ice Baby" has surged back to relevancy in recent years by branding himself as a fun-loving, dirt-bike-jumping, bong-ripping renegade of home renovation. When his music career hit a lull, he stacked cash by buying homes on the cheap, fancying them up, and then flipping them. That eventually became the premise of his award-winning reality show, The Vanilla Ice Project, which the DIY Network renewed earlier this year for a third season. B-list success begets B-list success. In recent months, he has been a judge on Canada Sings, worked his way into a feud between WWE's the Rock and John Cena, performed at halftime of a Minnesota Timberwolves game, and gone back to the studio — albeit with Psychopathic Records and the Insane Clown Posse. He's living the American juggalo dream.